Chiral approaches to several natural products, including the pseudomonic acids (with emphasis on pseudomonic acid C), colletodiol, and grahamimycin A1, are proposed. The primary approach to pseudomonic acid proceeds via use of a new carbon-carbon bond forming process to couple two complex appendages to a lyxose pyranoside. A well precedented back-up approach is also presented which does not rely on the new organometallic reaction. The proposed total synthesis of colletodiol is designed to lead to the naturally occurring enantiomer with (2R, 8R, 10R, 11S) chirality. An absolute configuration is proposed for the potent new antibiotic grahamimycin A1. A three step conversion of colletodiol to grahamimycin A1 is proposed to substantiate this proposal and provide a chiral synthesis of this novel antibiotic from readily available materials.